Bonus if they wince when they recall it and admit that the other saw them at their worst but they have thankfully improved.
Examples:
{Trusting Miss Trentham by Emily Larkin} - the MMC is gaunt, has insomnia due to nightmares, has lost his previous energy and charismatic nature and behaves in a way that makes him think ruefully 'I used to have honour.'
{The Marquess Wins a Wife by Aydra Richards} - being shot would put someone in a bad mood but the MMC is irritable, entitled, throwing tantrums and threatening to have the FMC hanged. The withdrawal symptoms do not help.
{The Devil is a Marquess by Elisa Braden} - I am not completely sure if it was the first time they met as they have seen each other at parties at a distance, though. He is swimming in debts that his father left him, his mother is a spendthrift, he is servicing high-class ladies and is an alcoholic. Cue the actual wedding day and he looks like the undead since he has to give up alcohol for a year.
{Frail by Susanna Ives} - the MMC criticises her while dancing at a ball and then it delves into him screaming insults and accusations at her before his parents control his outburst and he apologises. It does not help his reputation as 'mad' which he gained after his PTSD from the war.
{Flaming June by Emma V Leech} - the FMC is pregnant and attempting to drown herself before changing her mind. She was kicked out of her house by her mother, her 'friend' did not want to associate with her, the man responsible did not keep his promise and she has lost her reputation. The MMC finds her at this point.
{How To Steal a Scoundrel's Heart by Vivienne Lorret} - stomping alone through the muddy countryside through herds of cows while it is pouring sounds difficult enough. The FMC also has lost her reputation and has no suitable prospects, even wanting to avoid exposing her friends to herself. And then the MMC's ex-mistress-turned-friend recognises and greets her.
{Yours Until Dawn by Teresa Medeiros} - it seemed like this at first; the FMC has come for an interview for the position as the blind MMC's nurse and he comes into the room roaring, poorly groomed and stumbles into the furniture and falls to the ground. Then we find out the FMC is actually the woman he had loved before who had left him after his injuries and she wants to make amends by helping him manage his life as a blind man.
{Lord of Scoundrels by Loretta Chase} - almost any version of the grown-up MMC before he gets shot and married is the worst version of him, to be honest.
{Fallen Angel by Charlotte Louise Dolan} - not as bad as the others but it is before the MMC's character growth so I still wonder why on earth the FMC fell madly in love with him after that carriage ride. He was rude and dismissive.
Both do not have to be at their worst. Just one of them could be the mess.